Yarn treating process and composition therefor



patented Dec. 19, 1939 UNITED STATES PATENT OFFICE YARN TREATING PROCESS AND COM- POSITION THEREFOR Joseph .B. Dickey and James B. Normington,

Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application November 26, 1937,

. Serial No. 176,698

24 Claims.

This invention relates to the conditioning 'of textileyarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, etc., to render them more amenable to textile operations such as knitting and chanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. In addition,it is necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and.thus produce a closelyknit fabric free from such defects as stitch distortion, pin holes, "laddering, and the like.

Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and insome cases too drastic a solventaction on the yarn. Many of such agents possess slight or insuficient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softcalling and lubricating agents are insufficiently soluble in water to permit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarns composed of or containing W organic derivatives of cellulose and capable of lubricating, softening, and rendering such yarns more amenable to knitting and other textile operations. .A further and specific object is to provide a class of conditioning agents which augment or assist the lubricating action of various lubricants when applied to such yarns. A still further object is to provide yarn softening and lubricat-' ing formulas which can be readily removed from the yarns by the usual scour baths. A still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are em-' ployed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including knitting, weaving, spinning and the like. Still another object is to provide new chemical compounds having the structure and properties discussed below. Other objects will appear hereinafter.

These objects .are accomplished by the following invention which, in its broader aspects, comprises the discovery that acetals having the general formula: l

H OR;

where R is an alkyl, substituted alkyl or aryl, R1 is an aIkyL'substituted alkylor aryl, and R2 is an alkyl group, may be used as yarn conditioning agents and particularly as softening agents,- with or without the addition of animal, mineral or vegetable oils, in the treatment of yarns composed of or containing organic'derivatives of cellulose. We have found that these compounds have a slight solvent and/or softening action on cellulose organic derivative yarns which renders such yarns soft and pliable without at the same time having too drastic a solvent action thereon.

These compounds which are properly classifiable as acetals may be prepared from the mixed halogenated acetals, the preparation of which is described and claimed in our co-pending application Serial No. 213,027, filed June 10, 1938, using methods previously described in the literature. Examples of typical acetals of this type and their boiling points are given in the table below:

a-Tetrahydrofurfuryloxy-p-.

ethoxyethoxyethylether" B. P. 155-60/9 mm. a-Phenoxy-p-ethoxyethoxya Ethoxyethoxyethoxy p ethoxyethoxyethylether B. P. 165-'l5/9 mm. a-Methoxy- 3-ethoxyethoxy- J ethylether B. P. 85-90/ 10 mm. a-Tetrahydrofurfuryloxy-pt e t r a lnrdrofurfuryloxyethylether B. P. 170-80/ 9 mm.

In order to illustrate further the method of preparation of these compounds, examples of the preparation of two typical acetals of this classification are given.

Preparation of a-methoxz ethomyep-ethoazyethoxy- I ethyl ether One mole of sodium is dissolved in two moles of ethoxy ethanol and this solution treated while not with one mole of a-methoxyethoxy-p-chloroethylether. The mixture is stirred and refluxed for four hours. The product is then worked up in the usual way to give the desired ether, B. P. 129-34/ 10 mm.

Preparation of a a-di-tetrahydrofarjaryloxyetltyl ether One mole of a-tetrahydrofurfuryloxy-p-chloroethylether is dissolved in four moles of tetrahydrofurfuryl alcohol and heated on the steam bath. One mole of solid potassium hydroxide is then added in small portions with shaking.

Heating is continued for five hours to complete the reaction. The mixture is then allowed to stand several hours, is filtered and distilled.

. The desired ethyl ether is obtained in good yield,

B. P. 173-8/9 mm.

-In accordance with the invention these com- .pounds may be applied directly to the yarn dur- ,ing or after spinning, or may be added to the spinning solution itself. We have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may .be, and preferably are, employed as ingredients tate in acetone in which is incorporated 1-25%' by weight of a-tetrahydrofurfuryloxy-fl-ethoxyethylether is extruded through fine orifices into an evaporative atmosphere. The filaments thus produced are wouhd or twisted and wound.

Yarns produced from filaments thus prepared are pliable and suitable for knitting.

Example II.Yarn designed for knitting and composed to cellulose acetate is treated by applying thereto a-phenoxy -p-ethoxyethylether by means of an applicator roll. The amount of the conditioning liquid applied may run from 4 to by weight of the untreated yarn. If the yarn This composition is applied to a cellulose acetate yarn intended for knitting in an amount representing 4 to 25% by weight of the untreated yarn. The filaments or fibers treated as described above are quite soft and pliable and give excellent results in textile operations, especially in knitting.

Other examples of yarn conditioning compo- I sitions which may be applied to various types of yarn, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters, in accordance with our invention, and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are

the following:

Example IV:

. Parts aMethoxy p ethoxyethoxyethoxyethylether 60 Blown olive oil 40 Example V:

. Parts at Methoxyethoxy-p-tetrahy'drofurfuryloxyethylether Nea ts-foot oil 30 Example VI:

Parts oz Ethoxyethoxyethyl p ethoxyeth xyethylether i 70 Blown neats-foot oil 30 Example ,VII 3 v r 7 Parts a-Methoxy-,8-ethoxyethoxyethylether '10 Light mineral oil 30 ..Example VIII:

Parts a-Tetrahydrofurfuryloxy p tetrahydrofurfuryloxyethylether' Sperm il 50 Example IX:

Parts at Tetrahydrofurfuryloxy p ethoxyethoxyethylethern-uue '70 Blown sperm oil 30 Example X: y

I Parts a-Methoxyethoxy p ethoxyethoxyethylether 10 Water 80 Water soluble cellulose ester 5 Blown olive oil 5 hill As will be apparent from the above examples methods. For example, we may employ the agent as aningredient of the spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulose derivative used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

Ii the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll, or felt wet therewith or the liquid may be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like. or by the so-called bobbin to bobbin" method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn'such as a'yarn composed of cellulose acetate, is intended for knitting, about 4 to or more by weight, based on the weight of,the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples we have reierred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, nonsolvents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to coHtrol the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example, by reducing the amount of the agent and correspondingly increasing the amount of the oil or other ingredient.

While we have described our invention with M reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types.of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used herein and in the.

- the yarn material.

acteristic of these compounds is their exceptional claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together compositethreads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun tions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivativesof cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on Another outstanding charsolvent power for a Wide variety of mineral, animal and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due totheir'solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What we claim and desire to secure by Letters Patent of the United States is: r

1. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an acetal ether having the general formula:

where R is an organic radical selected from the group consisting of alkyl, aryl, and substituted alkyl groups,.R. is an organic radical selected from the group consisting of alkyl, aryl and subsituted alkyl groups, and R." is an alkyl group.

2. The process of conditioning yarn composed of or containing organicderivatives of cellulose to render it more amenable to textile operations including knitting, weaving, spinning and the like which-comprises applying thereto a lubricating and softening composition containing as its csknitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an-acetal ether having the general formula:

where R is an organic radical selected from the group consisting of alkyl, aryl, and substituted alkyl groups, R is an organic radical selected from the group consisting of alkyl, aryl and substituted alkyl groups, and R" is an alkyl group.

4. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinningand the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an acetal ether having the general formula:

where R is an organic'radical selected from the group consisting of alkyl, aryl, and substituted alkyl groups, R is an organic radical selected from the group consisting of alkyl, aryl and subf" stituted alkyl groups, and R" is an alkyl group.

and a textile lubricant.

5. The process of conditioningyarn to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an acetal ether having the general formula:

where R and R are organic radicals selected 60 from the group consisting of alkyl, aryl, tetrahydrofurfuryl, and substituted alkyl groups, and R" is an alkyl group.

6. The process of .conditioning yarn to render it more amenable to textile operations including 65 knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an acetal ether having the general formula:

where R and R are tetrahydrofurfuryl groups,' and R' is an alkyl group.

7. The process of conditioning yarn composed of or containing cellulose acetate to renderit more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a-tetrahydroiurfuryloxy-p-ethoxyethoxyethylether.

8. The process of conditioning yarn composed of or containing'cellulose acetate .to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a-DhGIlOXY- p-ethoxyethoxyethylether.

H on" where R is an organic radical selected from the group consisting of alkyl, aryl, and substituted alkyl groups, R is an organic radical selected from the group consisting of alkyl, aryl and substituted alkyl groups, and R" is an alkyl group.

11. A conditioning agent for rendering textile yarns composed of or containing organic derivatives of cellulose more amenable to textile operations including knitting, weaving, spinning and the like which comprises an acetal ether having the generalformula: I

R-O-CHa-C where R is an organic radical selected from .the group consisting of alkyl, aryl, and substituted alkyl groups, R is an organic radical selected from the group consisting of alkyl, aryl and substituted alkyl groups, and R" is an alkyl group, and a textile lubricant.

12. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving, spinning and the like which comprises an acetal ether having the general formula:

R-oomo 1 I OR" where R and R are organic radicals selected, from the group consisting of alkyl, aryl, tetrahydrofurfuryl, and substituted alkyl groups, and R" is an alkyl group. i t

13. A conditioning agent for rendering yarns more amenable to textile operations including knitting, weaving, spinning and the like which comprises an acetal ether having the general formula:

R-O-CHz-C whereR and R are tetrahydrofurfuryl groups, and R" is an alkyl group.

14. A conditioning agent for rendering yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing a tetrahydrofurfuryloxy ,3 ethoxyethoxyethylether.

15. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning and the like containing a-phenoxy-,9-ethoxyethoxyethylether.

16. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing or. tetrahydrofurfuryloxy p tetrahydrofurfuryloxyethylether.

17. Textile yarn amenable to textile operations including knitting, weaving, spinning and the like impregnated with a lubricant containing an acetal ether having the general formula:

n-o-om-c where R is an organic radical selected from the group consisting of alkyl, aryl, and substituted alkyl-groups, R is an organic radical selected from the group consisting of alkyl, aryl and substituted alkyl groups, and R" is an alkyl group,

18. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, and the like, empregnated with a conditioning agent comprising an acetal ether having the general formula:

where R and R are organic radicals selected from the group consisting of alkyl, aryl, tetrahydrofurfuryl, and substituted alkyl groups, and R" is an alkyl group.

21. Textile yarn amenable to textile operations including knitting, weaving, spinning, and the like impregnated with a lubricant containing an acetal ether having the general formula:

where R and R are tetrahydrofurfuryl groups, and R" is an alkyl group,

22. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising atetrahydrofurfuryloxy-p-ethoxyethoxyethylethen,

23. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising a-- phenoxy-fl-ethoxyethoxyethylether.

24. Textile yarns composed of or containing cellulose acetate amenable to textile operations including kitting, weaving, spinning, and the like,

. impregnated with a lubricant comprising a-tetrahydrofurfuryloxyp tetrahydrofuriuryloxyethylether.

JOSEPH B. DICKEYRL JAMES B. NORMINGTON. 

